Methyl iodide → 7-(Methyloxy)-1-(2-propen-1-yl)-1,8-naphthyridin-2(1H)-one

HRID 656886Notes

Reaction equation

HRID 656886 reaction equation
[CH2:1]([N:4]1[C:13]2[NH:12][C:11](=[O:14])[CH:10]=[CH:9][C:8]=2[CH:7]=[CH:6][C:5]1=[O:15])[CH:2]=[CH2:3].[CH3:16]C(C)([O-])C.[K+].C1COCC1.CI>CN(C=O)C>[CH3:16][O:14][C:11]1[N:12]=[C:13]2[C:8]([CH:7]=[CH:6][C:5](=[O:15])[N:4]2[CH2:1][CH:2]=[CH2:3])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 688165451-(2-Propen-1-yl)-1,8-naphthyridine-2,7(1H,8H)-dione

Product 1

HCID 688163437-(Methyloxy)-1-(2-propen-1-yl)-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(2-propen-1-yl)-1,8-naphthyridine-2,7(1H,8H)-dione (123 mg, 0.61 mmol) in DMF (2 ml) was treated under argon with a solution of potassium t-butoxide in THF (1M; 0.7 ml, 0.7 mmol) then methyl iodide (0.06 ml, 142 mg, 1 mmol) was added. After 30 minutes the mixture was evaporated and the residue chromatographed eluting with 0-100% ethyl acetate in hexane affording an oil (120 mg, 92%).

Workup

  1. customAfter 30 minutes the mixture was evaporated
  2. customthe residue chromatographed
  3. washeluting with 0-100% ethyl acetate in hexane affording an oil (120 mg, 92%)

Sources & evidence

ORD record
ord-3ae095141f1b4fcabc9d77aa52c6b9c1
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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